7 Crushing Mistakes That Left Her Heartbroken


If you’ve been heartbroken, sometimes there is nothing you could have done differently that would change the outcome.

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Occasionally, women do make dating mistakes that push a guy away. Discover my advice on handling this disastrous dating situation.


“Dear Ronnie The Dating Coach for Women Over 40,

I’ve had a crush on his guy for 4 months and few weeks ago he finally ask me out. He wined and dined me. Even went early to go pick up the movie tickets. The next day he texted me saying he forget to give me something and asked to drop by to give it to me. It was a pink rose. We ended up go get take out and came back for movie marathon at my place. He stayed the night.

I can for sure tell he was heading towards relationship with me. He was even willing to take one day off to go to New York with me for my photo shoot. We text and talk during the week. The downhill came when I was going out of town the following weekend.  I asked him if he’d like to see me before I leave. Initially we planned lunch but it didn’t work out. That night he was suppose to watch a game with his cousin, but instead he invited me to watch it with him instead. And I ended up stay over night again. We were up all night and by the time we looked at the clock, he had to go to work.

I asked, “Where is this going?” He said,“I can’t think right now. I didn’t sleep all night and now I have to go to work.” Later  he called me to say he is not looking for relationship because of his family problems and financial issue.

Saturday, he texted me, then  called when I didn’t respond, but I missed his call. Then Sunday morning I did the most out of character thing I ever did. I called him up at 8 am and said told him he seemed was different. I asked why none of my Prince Charmings are looking for a relationship.

Then Monday came around and I felt bad so I called him. He took time to clear things up with me. I apologized, explaining that I feel like I get played a lot. He said he had no intention of playing me, he just enjoyed my company, but he is not emotionally stable. We haven’t talked since.

So now my question is should I move on? Will he come back around ? Was that talk a goodbye? I really like this guy a lot. I like him the first movement I saw him and now I feel heartbroken. Please help me. I am feeling powerless which I haven’t had that feeling for long time. Usually I bounce back right away.

Thank you!
Powerless Gal”


Dear Powerless,

I know this might be hard to hear, but several things went wrong here that lead to feeling heartbroken:

  1. The whole “stopping by with a gift” thing was a play to get you into bed – it worked.
  2. Just because a man shows amazing interest doesn’t mean he wants to get into a relationship. But he may want to get into your pants.
  3. It’s best to hold off on s.e.x, not because it’s wrong, but to guard your heart from hurt should the guy disappear.
  4. It’s also works best to let men lead. So asking him if you can get to get together before you went away wasn’t letting him lead. It would have been better to let him miss you and then want to see you. Instead, you pursued him by asking to see him. For the first 4-8 dates, let the man initiate so you can learn how much he wants to see you. If you ask, you’ll never know if he’s being polite or truly interested.
  5. When a man tells you he’s not looking for a relationship, BELIEVE HIM. He’s not ready and he told you so.
  6. Never ask a man, “Where is this going?” after only two dates or even four. That’s a conversation after dating consistently for at least four to six months, depending on your age. If you’re younger (20’s) it could be more like six-eight months.
  7. Try not to get so excited about a man you only had a couple of dates with. No matter how much fun you had, it’s easy to see that things do not always progress or turn into a relationship. This is why I recommend dating more than one man at a time. You never know who will stick around and who will disappear as fast as he came on. This strategy helps you stay emotionally balanced instead of getting over the top too soon. That’s what leads to heartbreak.

Based on these seven mistakes and the final outcome, I can guarantee he is not the right man for you. He may seem like a great guy with desirable qualities, but he doesn’t want a relationship. There’s no way to bridge that gap. More heartbreak will follow if you continue to go after him. The hard truth is, even if you had not made these mistakes, he would still be the wrong guy because he’s not looking for a relationship.

In a way, you are lucky you made these dating mistakes with this guy since there was little risk of ruining a good thing. Learn from this situation so you don’t repeat these devastating errors.


Keep this in mind – the biggest mistake you made was getting so attached before you knew he was a keeper. That’s the true cause of the heartbreak you feel.


Absolutely move on to find a man who is relationship ready and not full of excuses.


Wishing you love,

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Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony, MSN.com, MORE.com, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

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